My Ideal East Coast Road Trip Itinerary!

Hello from España! I am currently living in Madrid and will be here for the next month. This is just the beginning of a 9 month European adventure, so get ready for some awesome content! For now, enjoy this wonderful guest post by Kacey Mya. More details on her below!

The West Coast gets all the attention when it comes to road trips, but, me? I dream of driving down the East Coast.

The East Coast has it all: big cities, beaches, small towns, mountains and even a kitschy attraction or two. I know because I’ve been devising my own dream road trip for years. And, in order to prove just how amazing an East Coast road trip would be, I’m going to share that itinerary here:

1. Portland, Maine: There’s no better place to start than picturesque coastal Maine. A few plates of fresh Lobster (or a half-dozen lobster rolls) will give you all the protein you need to power you through the first leg of your journey. 

2. Salem, Massachusetts: You have probably heard about the Salem Witch Trials — don’t worry, they’re long over. But Salem still capitalizes on its weird history of “witchcraft” with reenactments, museums and other related landmarks. It might seem a bit cheesy, and it is; but it’s also a fun and memorable place to stop on your trip down the coast.

3. Washington, D.C.: You can take in a bit more national history here. There’s also an incredible roster of museums in the city if you happen to get there on a rainy day.

4. Boston, Massachusetts: No East Coast road trip would be complete without a trip to Boston. Seriously, there’s so much history here that you could dedicate an entire trip to this Northeastern city. And, depending on how long you’re dedicating to your road trip, you could stay a bit longer and see it all. 

5. Newport, Rhode Island: A nice pause between the two of the most major cities on this list, Newport has always been a summer playground for the rich and fabulous. In fact, John F. Kennedy used to vacation here during his time in the White House. 

6. New York, New York: If you take a look at some of the best road trips, a lot of them will have you starting here, and for good reason: who doesn’t dream of visiting the Big Apple? Like Boston, you can stay here for days or weeks, even, and never run out of things to do — or bagels and pizzas to eat.

7. Atlantic City, New Jersey: Atlantic City is a great overnight stop since it’s jam-packed with casinos and clubs. Let your hair down before you get back on the road to… 

8. Philadelphia, Pennsylvania: The City of Brotherly Love! It’s another must-see since, you know, our nation started here. Grab a cheesesteak and see the sights in a day. 

9. Williamsburg, Virginia: In Williamsburg, you can do one of two things: break up your historically fueled stops at the Busch Gardens theme park, or keep the learning going by stopping into Colonial Williamsburg, a living history museum which replicates 18th-century life. 

10. Wilmington, North Carolina: Now, let’s start our tour of the East Coast’s best coastal cities. Wilmington, North Carolina has access to wonderful beaches, but, if you’re a movie or TV buff, you can also visit the sites where shows like One Tree Hill and Dawson’s Creek were filmed. 

11. Charleston, South Carolina: Charleston exudes old Southern vibes, from its old, shady trees to its famous colonial houses. You can also eat really well here, as the culinary scene is alive and very well, especially when it comes to southern cuisine. 

12. Savannah, Georgia: Savannah has the same level of Southern charm as Charleston, with its pre-Civil War architecture and horse-drawn carriages. It’s also legal to drink adult beverages on the street of the historic downtown district, so you might want to plan to sleep in after your stop here. 

13. Amelia Island, Florida: After a rousing evening in Savannah, head to Amelia Island for a lazy day on the beach. You might also want to explore the marshlands, hit the links or dig into fresh seafood… 

14. Orlando, Florida: Between Disney World and Universal Studios, you will find one amusement park that you want to visit — now, let’s all give ourselves a day to act like kids again. 

15. Miami, Florida: Miami has so much culture and a lively nightlife scene to match. And then, of course, there are the beaches. 

16. And, if you’re not yet sick of driving… Key West, Florida: I realize the end of this trip is pretty beach-heavy, but it’s nice to relax between long stretches of driving. Key West’s funky, eclectic culture — and white-sand beaches that ease into clear water — will make it a great last stop on your journey.

There’s no wrong or right way to do a road trip, and my dream itinerary is just one way to make it happen. Highlight the places you have to see, throw a few of mine in there and voila: you’re on your way to a lifetime of memories made behind the wheel.


About the author: Kacey is a lifestyle blogger for The Drifter Collective, an eclectic lifestyle blog that expresses various forms of style through the influence of culture and the world around us. Kacey graduated with a degree in Communications while working for a lifestyle magazine. She has been able to fully embrace herself with the knowledge of nature, the power of exploring other locations and cultures, all while portraying her love for the world around her through her visually pleasing, culturally embracing and inspiring posts.

You can follow her on Twitter, Pinterest, and Instagram!


  1. Rachel Elizabeth says:

    Whoa, this is such a comprehensive list! I live in NJ so I have been to a lot of these places – especially Philadelphia and New York City. And Atlantic City is definitely a fun time at the casinos! I always seem to lose money, though, argh!

  2. Tamara Elliott says:

    This would be an amazing itinerary! I think pretty much every road trip has the potential to be fun, but the list you’ve put together here definitely hits some great spots.

  3. Tom says:

    I live on the east coast, and I still haven’t seen all these places yet. The northern part is quite easy, all places are fairly close, but distances spread out once you get south of DC.

  4. Michelle W says:

    This is an amazing itinerary! And you’re right, why do people always exclusively associate the western US with roadtrips? I think this one almost intrigues me more because of the amazing historic value to many of these places. Also I just finished reading the book “Salem 1692” and now I really do need to get there!

  5. TravellingDany says:

    I haven’t been in Madrid for so long and I can’t wait to read more about it!
    As for the East Coast tour… kudos for adding Salem too!!! Here people keep on forgetting it even exists, they are genuinely ignorant about the real story!

    • Lauren Meshkin says:

      You don’t have to do this all in one road trip but if you DID – I would say at least a few weeks! I absolutely love Charleston. I haven’t visited Colonial Williamsburg since I was young.

  6. Lydia@LifeUntraveled says:

    Wow that’s quite the road trip! I live in Montreal (Quebec) so it would be easy for me to head across the border to start my journey. It must be amazing to see the ever-changing scenery along the way!

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